PL10604B3 - Process for the preparation of disodium salts of sulfo-methyl-amino-metallo-mercapto-sulfonic acids. - Google Patents
Process for the preparation of disodium salts of sulfo-methyl-amino-metallo-mercapto-sulfonic acids. Download PDFInfo
- Publication number
- PL10604B3 PL10604B3 PL10604A PL1060427A PL10604B3 PL 10604 B3 PL10604 B3 PL 10604B3 PL 10604 A PL10604 A PL 10604A PL 1060427 A PL1060427 A PL 1060427A PL 10604 B3 PL10604 B3 PL 10604B3
- Authority
- PL
- Poland
- Prior art keywords
- mercapto
- amino
- methyl
- metallo
- sulfonic acids
- Prior art date
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- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 title description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- -1 disulphite compound Chemical class 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XLNOKJLJDWVOQP-UHFFFAOYSA-L disodium;formaldehyde;sulfite Chemical compound [Na+].[Na+].O=C.[O-]S([O-])=O XLNOKJLJDWVOQP-UHFFFAOYSA-L 0.000 description 1
- DXRFSTNITSDOKK-UHFFFAOYSA-N formaldehyde;sulfurous acid Chemical compound O=C.OS(O)=O DXRFSTNITSDOKK-UHFFFAOYSA-N 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
Description
Najdluzszy czas trwania patentu do 13 marca 1944 r.Wedlug patentu Nr 10168 otrzymuje sie sole dwusodowe kwasów 4-amino-metyleno- siarkawo-2-metalo-merkapto-benzeno-./-sul- fonowych lub inaczej kwasów ^nsulfono- metylo-ainino-Z^etaloHmerkapfto-benzeiio- i-sulfonowych ma drodze dzialania .siarczy¬ nem fortmaldehydo-sodowym na sole sodo¬ we kwasów 4-ammo-2-metalo-merkapto- benzeno-f-sulfonowych.Okazalo sie, ze wedlug podobnych spo¬ sobów mozna tez przeprowadzic i inne kwasy amino-metalo-merkapto-sulfonowe w odpowiednie zwiazki suifo-metylo-ami- nowe.Nowe te zwiazki maja sluzyc do celów terapeutycznych i w porównaniu z mate¬ rialami wyjsciowemu wyrózniaja sie swo¬ ja trwaloscia oraz nieszkodliwoscia dla zdrowia. Zwiazki te sa w wodzie bardzo latwo rozpuszczalne.Przyklad L 37,6 czesci soli sodowej kwasu ammo-zlotowo-merkapto-etamo-sul- fomowego (otrzymanej z kwasu aimino-chlo- ro-etanoHsulfonowego (Berichte 15,446) przez traktowanie alkoholowym roztworem kwasnego siarczanu potasowego i wprowa¬ dzenie zlota) rozpuszcza sie w 150 cze¬ sciach wody, dodaje 15 czesci siarczynu fonmaldehydo-sodowego i ogrzewa otrzy¬ many w ten sposób roztwór do 90°, Po o-chlodzeniu wytraca sie zapomoca alkoholu metylowego powstaly zwiazek dwusiarczy- no^formajdehydtfwjf, -Ni»-.* Zwiazek* ten jelt proszkiem laitwo roz¬ puszczalnym w wodzie, nieco zabarwionym, posiadajacym 39% zlota.Przyklad II. Rozpoiszcza sie 42,3 cze¬ sci soli sodowej kwasu 4-amino-2-zlotowo- merkajpto-benzeno-./-sulfonowego (otrzynia- manej z kwasu 3-nitro-anilmo-6-sulfonowe- go przez dwuazowanie, rozlozeniem pro¬ duktu dwuazowania rodankiem potasowym, zredukowaniem otrzymanego kwasu 3-nitro- 1 - rodano ? benzenu- 6 - (sulfonowego oraz wprowadzenie zlota) w 200 czesciach wo¬ dy, wprowadza 13 czesci siarczynu formal- dehydo-isodowego i ogrzewa powstaly w ten sposób roztwór do wrzenia przy jednoczes- nem wstrzasaniu. Nastepnie zostawia sie do ochlodzenia i wytraca utworzony zwia¬ zek dwusiarczyno-formaldehydowy zapo¬ moca alkoholu. Zwiazek ten rozpuszcza sie latwo w wodzie i posiada 36% zlota.Przyklad III. Rozpuszcza sie 33,4 cze¬ sci 4-amino-2-srebrowo-merkcipto-benzeno- 1 -sulfonianu sodowego w 16 czesciach wo¬ dy, wprowadza 15 czesci siarczynu formal- dehydo-sodowego i ogrzewa powstaly w ten sposób roztwór do wrzenia, przy jedno- czesnem wstrzasaniu. Pozostawia sie do o- chlodzenia i wytraca powstaly zwiazek formaldehydo-siarczynowy zapomoca alko¬ holu. Jest on bardzo latwo rozpuszczalny w wodzie i posiada 24% srebra. PLThe longest duration of the patent until March 13, 1944 According to patent No. 10168, disodium salts of 4-amino-methylenesulfuric-2-metallo-mercapto-benzene / sulfonic acids or in other words of nsulfon-methyl-ainino acids are obtained -Z-ethaloHmercapto-benzene-i-sulfonic acid by the action of sodium fortmaldehyde sulfite on the sodium salts of 4-ammo-2-metallo-mercapto-benzene-f-sulfonic acids. Other amino-metal-mercapto-sulfonic acids can also be converted into corresponding suipho-methyl-amine compounds. These new compounds are intended to be used for therapeutic purposes and, compared to the starting materials, they are distinguished by their durability and harmlessness to health. . These compounds are very easily soluble in water. Example L 37.6 parts of sodium ammo-gold-mercapto-ethamosulfonic acid (obtained from amino-chloro-ethaneHsulfonic acid (Berichte 15.446) by treatment with an alcoholic solution of acid sulfate potassium and the introduction of gold) is dissolved in 150 parts of water, 15 parts of sodium phonmaldehyde sulphite are added and the solution obtained in this way is heated to 90 °. After cooling, the resulting disulphite compound is removed with methyl alcohol. ^ formajdehydtfwjf, -Ni »-. * Compound * this intestine is a powder easily soluble in water, slightly colored, having 39% gold. Example II. Solubilize 42.3 parts of the sodium salt of 4-amino-2-golden-mercajptobenzene / sulfonic acid (obtained from 3-nitro-anilmo-6-sulfonic acid by diazotization, staggering the proportions). of the diazotization product with potassium rhodate, reducing the obtained 3-nitro-1-rhodano-benzene-6 - acid (sulfonic acid and introducing gold) in 200 parts of water, introducing 13 parts of formaldehyde-iodine sulphite and heating the resulting solution to It is then allowed to cool and the formed disulphite-formaldehyde compound is destroyed with alcohol. This compound dissolves easily in water and has 36% gold. Example III. 33.4 parts are dissolved. Sodium 4-amino-2-silver-mercapto-benzene-1-sulfonate in 16 parts of water, introduces 15 parts of sodium formaldehyde sulfite and heating the resulting solution to the boil, while shaking it. until it cools down and removes any residual water formaldehyde-sulphite zeal in the form of an alcohol. It is very easily soluble in water and has 24% silver. PL
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| Publication Number | Publication Date |
|---|---|
| PL10604B3 true PL10604B3 (en) | 1929-08-31 |
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